Polymeric compositions and related methods of use

a polymer composition and composition technology, applied in the field of moussel adhesives, can solve the problems of complex synthetic procedures, no surface modification strategy that can be universally applied, and current methods rely on expensive instruments

Inactive Publication Date: 2005-12-29
NORTHWESTERN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0006] The present invention are compositions which function e.g., as an adhesive, in a substantially aqueous environment. The preferred composition...

Problems solved by technology

No surface modification strategy exists that can be universally applied to different classes of materials...

Method used

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  • Polymeric compositions and related methods of use
  • Polymeric compositions and related methods of use
  • Polymeric compositions and related methods of use

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Succinimidyl Carbonate PAO, SC-PAO7

[0168] PLURONIC® F 127 (0.60 mmols) was dissolved in 30 mL of dry dioxane. N,N′-Disuccinimidyl carbonate (6.0 mmols) in 10 mL dry acetone was added. DMAP (6.0 mmols) was dissolved in 10 mL dry acetone and added slowly under magnetic stirring. Activation proceeded 6 hours at room temperature, after which SC-PAO7 was precipitated into ether. The disappearance of the starting materials during the reaction was followed by TLC in chloroform-methanol (5:1) solvent system. The product was purified by dissolution in acetone and precipitation with ether four times. The product yield was 65%. 1H NMR (500 MHz, CDCl3): δ ppm 0.96-1.68 (br, —OCHCH3CH2O—), 2.80 (s, —COON(CO)2(CH2)2), 3.15-4.01 (br, —OCH2CH2O—; —OCHCH3CH2O—), 4.40 (s, —OCH2CH2OCOON(CO)2CH2CH2—).

example 2

Synthesis of DME-PAO7

[0169] A slurry of DOPA methyl ester hydrochloride (1.25 mmols) and triethylamine (2.5 mmols) was mixed with SC-PAO7 (0.16 mmols) in 10 mL chloroform. The disappearance of the starting materials during the reaction was followed by TLC in chloroform-methanol-acetic acid (5:3:1) solvent system. After stirring for 1 hour at room temperature, the solvent was evaporated off, and DME-PAO7 was purified by precipitation from cold methanol three times. DME-PAO7 gave a positive Arnow test indicating the presence of catechol hydroxyl groups. The product yield was 75%.

[0170]1H NMR (500 MHz, CDCl3): δ ppm 0.98-1.71 (br, —OCHCH3CH2O—), 2.83-3.06 (m, —NHCHCH2C6H3(OH)2COOCH3), 3.15-4.02 (br, —OCH2CH2O—; —NHCH(CH2C6H3(OH)2COOCH3), 4.05-4.35 (d, —OCH2CH2OCONHCHCH2C6H3(OH)2COOCH3), 4.55 (br, —NHCHCH2C6H3(OH)2COOCH3), 5.30 (d, —NHCHCH2C6H3(OH)2COOCH3), 6.45-6.80 (1s, 2d, —NHCHCH2C6H3(OH)2COOCH3).

example 3

Synthesis of DOPA-PAO7

[0171] L-DOPA (1.56 mmols) was added to 30 mL 0.1 M Na2B4O7 (pH=9.32) aqueous solution under Ar atmosphere, followed by stirring at room temperature for 30 minutes. SC-PAO7 (0.156 mmols) in 5 mL acetone was added to the resulting mixture and stirred overnight at room temperature. The solution pH was maintained with sodium carbonate during the reaction. The disappearance of the starting materials during the reaction was followed by TLC in chloroform-methanol-acetic acid (5:3:1) solvent system. The solution was acidified to pH 2 with concentrated hydrochloric acid and then extracted three times with dichloromethane. The combined dichloromethane extracts were dried with anhydrous sodium sulfate and filtered, and dichloromethane was evaporated. The product was further purified by precipitation from cold methanol. DOPA-PAO7 gave a positive Arnow test indicating the presence of catechol hydroxyl groups. The product yield was 52%. 1H NMR (500 MHz, CDCl3): δ ppm 0.92-...

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Abstract

Adhesive polymeric compositions which can comprise dihydroxyphenyl moieties and derivatives thereof, and related methods of use.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application is a continuation-in-part of U.S. Ser. No. 10 / 199,960 filed Jul. 19, 2002 which claimed priority to U.S. Ser. Nos. 60 / 306,750 and 60 / 373,919 filed, respectively, on Jul. 20, 2001 and Apr. 19, 2002. This application also claims priority to U.S. Ser. No. 60 / 548,314 filed Feb. 27, 2004, U.S. Ser. No. 60 / 549,259 filed Mar. 2, 2004. Each application is incorporated herein by reference in its entirety.STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT [0002] The United States Government has certain rights to this invention pursuant to Grant Nos. DE13030, DE12599 and DE14193 from the National Institutes of Health to Northwestern University and Grant No. NCC-1-02097 from NASA to Northwestern University.BACKGROUND OF THE INVENTION [0003] Mussel adhesive proteins (MAPs) are remarkable underwater adhesive materials that form tenacious bonds between mussels and the surfaces upon which the mussels reside. During the pro...

Claims

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Application Information

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IPC IPC(8): C08L89/00
CPCA61L24/046C08G65/3331C08G65/33317C08G65/33396C09J171/02C09J201/06C08L71/02C08L101/02
Inventor MESSERSMITH, PHILLIP B.DALSIN, JEFFREYLIN, LIJUNLEE, BRUCE P.HUANG, KUL
Owner NORTHWESTERN UNIV
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